JP2008536992A - Pigment composition - Google Patents

Pigment composition Download PDF

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JP2008536992A
JP2008536992A JP2008507054A JP2008507054A JP2008536992A JP 2008536992 A JP2008536992 A JP 2008536992A JP 2008507054 A JP2008507054 A JP 2008507054A JP 2008507054 A JP2008507054 A JP 2008507054A JP 2008536992 A JP2008536992 A JP 2008536992A
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pigment
polymer
pigment composition
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particles
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JP4666535B2 (en
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ルイス・ゴメス，グロリア
ビュニョン，フィリップ
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BASF Schweiz AG
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Ciba Holding AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/002—Influencing the physical properties by treatment with an amine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0011—Coated particulate pigments or dyes with organic coatings containing amine derivatives, e.g. polyamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/20—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the process features
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/41—Polymers attached to the pigment surface
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine

Abstract

本発明は、オリゴマーもしくはポリマーのアミンで処理されたか、またはポリマー中に封入された顔料（Ａ）を含む顔料組成物、その製造方法、ならびに着色プラスチックまたは着色ポリマー粒子製造におけるその使用に関する。  The present invention relates to a pigment composition comprising a pigment (A) treated with an oligomeric or polymeric amine or encapsulated in a polymer, a process for its production and its use in the production of colored plastics or colored polymer particles.

Description

本発明は、新規な顔料組成物、その製造方法、および着色プラスチックまたは着色ポリマー粒子、特にポリアミドを主成分とするものの製造におけるその使用に関する。   The present invention relates to a novel pigment composition, its production process and its use in the production of colored plastics or colored polymer particles, in particular those based on polyamide.

ポリアミドを主成分とするプラスチックの原液着色は、通常、高い加工温度でポリアミド素材に溶解し、そして不可欠な高い耐熱性を有することのほかに、ポリアミド溶融物の高還元性媒体に対する十分な化学安定性も有する、いわゆる油溶性染料を用いて行う。   Stock solution coloring of polyamide-based plastics usually dissolves in polyamide materials at high processing temperatures and has the essential high heat resistance, as well as sufficient chemical stability of polyamide melts against highly reducing media The so-called oil-soluble dye having a property is also used.

顔料の使用は、ほぼ例外なく、そのほとんどが重金属を含有する無機顔料と、主にフタロシアニンまたはキナクリドン類からの特定の有機顔料の極めてわずかな選択とに限られている。しかし、それらの有機顔料の多くは、特定の欠点、たとえばそれらの溶解性、ポリマーとの相互作用、または分解する傾向を有し、そして完成した着色ポリアミド材料は多くの場合蛍光を発する傾向を有する。   The use of pigments is almost exclusively limited to inorganic pigments, most of which contain heavy metals, and a very small selection of specific organic pigments mainly from phthalocyanines or quinacridones. However, many of these organic pigments have certain drawbacks, such as their solubility, interaction with the polymer, or a tendency to decompose, and the finished colored polyamide material often has a tendency to fluoresce .

したがって、たとえば、米国特許第４，０３１，０６０号には、ポリアミドの着色にＴｉＯ2を用いることが開示されている。 Thus, for example, US Pat. No. 4,031,060 discloses the use of TiO 2 for coloring polyamides.

このために、原液着色されたポリアミド材料において、耐光堅牢性であり高温耐光堅牢度を有する、強く着色された非蛍光の色合いをもたらし、そして全面的に良好な堅牢性を示す、新規な顔料または顔料組成物が必要とされている。   To this end, a new pigment or a solid pigmented polyamide material that is light-fast and has a high color fastness, has a strongly colored non-fluorescent shade and exhibits good fastness overall. There is a need for pigment compositions.

驚くべきことには、本発明による顔料組成物が上述の基準を大幅に満たすことが今や見出された。   Surprisingly, it has now been found that the pigment compositions according to the invention greatly fulfill the above mentioned criteria.

したがって、本発明は、顔料（Ａ）を含む顔料組成物であって、顔料（Ａ）が、オリゴマーもしくはポリマーのアミンで処理されたか、またはポリマー中に封入されている顔料組成物に関する。   Accordingly, the present invention relates to a pigment composition comprising the pigment (A), wherein the pigment (A) is treated with an oligomer or polymer amine or encapsulated in a polymer.

本発明による組成物に用いる顔料（Ａ）として、ジケトピロロピロール、アゾ顔料、キナクリドン、キノフタロン、フタロシアニン、インダントロン、フラバントロン、ピラントロン、アントラキノン、ペリレン、ジオキサジン、ペリノン、チオインジゴ、イソインドリン、プテリジン、イソインドリノンおよび金属錯体類から選択される任意の顔料が適切である。   As pigment (A) used in the composition according to the present invention, diketopyrrolopyrrole, azo pigment, quinacridone, quinophthalone, phthalocyanine, indanthrone, flavantron, pyrantrone, anthraquinone, perylene, dioxazine, perinone, thioindigo, isoindoline, pteridine, Any pigment selected from isoindolinone and metal complexes is suitable.

フタロシアニン、イソインドリノン、アゾおよびジケトピロロピロール顔料の使用が好ましい。   Preference is given to using phthalocyanine, isoindolinone, azo and diketopyrrolopyrrole pigments.

重要なのは、式：   The important thing is the formula:

Figure 2008536992

Figure 2008536992
Figure 2008536992
Figure 2008536992

の顔料である。 It is a pigment.

顔料の比表面積は、１０〜１５０m2/gであるのが好ましい。 The specific surface area of the pigment is preferably 10 to 150 m 2 / g.

比表面積が１２〜５０m2/gである不透明な顔料、および比表面積が５０〜１００m2/gである透明な顔料が特に好ましい。 Opaque pigment having a specific surface area of 12~50m 2 / g, and specific surface area is particularly preferable transparent pigment is 50 to 100 m 2 / g.

本発明による顔料組成物の製造には、オリゴマーもしくはポリマーのアミンとして、末端アミン官能基を有し、場合により変わりうる数の第二級アミノ基で中断された飽和炭化水素鎖から作られた化合物を用いる。   For the preparation of pigment compositions according to the invention, compounds made from saturated hydrocarbon chains with terminal amine functional groups and optionally interrupted with a variable number of secondary amino groups as oligomeric or polymeric amines Is used.

このような化合物の例は、ポリエチレンイミン、アルキルジエチレントリアミン、アルキルトリエチレンテトラミン、アルキルジプロピレントリアミン、アルキルトリプロピレンテトラミン、アルコキシトリアミン、アルコキシテトラミンおよびビニルアミンポリマーを含む。   Examples of such compounds include polyethyleneimine, alkyldiethylenetriamine, alkyltriethylenetetramine, alkyldipropylenetriamine, alkyltripropylenetetramine, alkoxytriamine, alkoxytetramine and vinylamine polymers.

オリゴマーもしくはポリマーのアミンの中で、次の化合物が特に重要である：Ｎ−タロウアルキルジプロピレントリアミン、Ｎ−タロウアルキルジプロピレンテトラミン、Ｎ，Ｎ，Ｎ’Ｎ’−テトラメチルエチレンジアミン、ココジプロピレントリアミン、オレイルジプロピレントリアミン、ドデシルジプロピレントリアミンおよびオレイルトリプロピレンテトラミン。   Of the oligomeric or polymeric amines, the following compounds are particularly important: N-tallowalkyldipropylenetriamine, N-tallowalkyldipropylenetetramine, N, N, N′N′-tetramethylethylenediamine, cocodipropylene. Triamine, oleyl dipropylene triamine, dodecyl dipropylene triamine and oleyl tripropylene tetramine.

本発明による顔料組成物を製造するために、顔料粒子を、オリゴマーもしくはポリマーのアミンそれ自体と共に、またはそのアミンを含有する溶液と共にスプレーし、そして乾燥するか、あるいは顔料粒子をオリゴマーもしくはポリマーのアミンまたはオリゴマーもしくはポリマーのアミンを含有する液体に浸漬し、処理した顔料粒子をろ別し乾燥するか、またはスプレー乾燥する。   To produce the pigment composition according to the invention, the pigment particles are sprayed with the oligomer or polymer amine itself or with a solution containing the amine and dried, or the pigment particles are oligomer or polymer amine. Alternatively, it is immersed in a liquid containing oligomeric or polymeric amine and the treated pigment particles are filtered off and dried or spray dried.

処理する顔料に対するオリゴマーもしくはポリマーのアミン（中性または第４級）の量は、顔料の重量に基づいて、オリゴマーアミン２〜５００重量％、好ましくは１０〜１００重量％、およびポリマーアミン１０〜２００重量％の広い範囲内で変えることができる。   The amount of oligomeric or polymeric amine (neutral or quaternary) relative to the pigment to be treated is 2 to 500 wt% oligomeric amine, preferably 10 to 100 wt%, and 10 to 200 polymeric amine based on the weight of the pigment. It can be varied within a wide range of weight percent.

顔料のいわゆる封入には、原則的に、天然物、または好ましくは様々な種類の、重合、重付加もしくは重縮合の合成生成物、たとえばポリエステル、ポリエーテル、ポリアミド、ポリイミド、ポリ尿素、ポリウレタン、ポリスルフィド、ポリオレフィン、ポリ（メタ）アクリレート、ポリ（メタ）アクリルアミド、ポリ酢酸ビニル、ポリエチレンイミン、ポリアミン、ポリアルコール、ポリグリコール、ポリグリコールエステル、ポリカルボン酸、ポリスチレン、ならびに上述したポリマーを含有する混合ポリマー、ならびにコポリマーおよびターポリマーを用いることができ、アクリル酸、メタクリル酸、アクリルアミド、メタクリルアミド、スチレンまたはウレタンを主成分とするホモポリマー、コポリマーまたはターポリマーを用いるのが有利である。   For the so-called encapsulation of pigments, in principle, natural products or preferably various types of synthetic products of polymerization, polyaddition or polycondensation, for example polyesters, polyethers, polyamides, polyimides, polyureas, polyurethanes, polysulfides. , Polyolefins, poly (meth) acrylates, poly (meth) acrylamides, polyvinyl acetate, polyethyleneimines, polyamines, polyalcohols, polyglycols, polyglycol esters, polycarboxylic acids, polystyrenes, and mixed polymers containing the above-described polymers, As well as copolymers and terpolymers, homopolymers, copolymers or terpolymers based on acrylic acid, methacrylic acid, acrylamide, methacrylamide, styrene or urethane. It is advantageous.

封入には、ポリアクリル酸アンモニウム、ナトリウム、カルシウム、アルミニウム、亜鉛もしくはジルコニウム、アクリル酸エステルまたは（メタ）アクリル酸／スチレンコポリマーの使用が好ましい。   For encapsulation, the use of ammonium polyacrylate, sodium, calcium, aluminum, zinc or zirconium, acrylate esters or (meth) acrylic acid / styrene copolymers is preferred.

アンモニウムは、基+ＮＲ1Ｒ2Ｒ3Ｒ4（式中、Ｒ1〜Ｒ4は、互いに独立に、水素またはＣ1〜Ｃ18アルキルである）であることが理解される。 It is understood that ammonium is a group + NR 1 R 2 R 3 R 4 where R 1 -R 4 are independently of one another hydrogen or C 1 -C 18 alkyl.

用いるポリマーは、平均分子量が２０００〜５００００g/mol、特に２０００〜１２０００g/molであるのが好ましい。   The polymer to be used preferably has an average molecular weight of 2000 to 50000 g / mol, particularly 2000 to 12000 g / mol.

本発明による顔料組成物を封入によって製造する場合、顔料粒子をポリマーと共にまたはポリマーを含有する溶液と共にスプレーし、乾燥するか、あるいは顔料粒子を、ポリマーまたはポリマーを含有する液体に浸漬し、処理した顔料粒子を場合により、たとえばｐＨの変更または溶剤の添加によって沈殿させ、ろ別し乾燥するか、またはスプレー乾燥する。   When the pigment composition according to the invention is produced by encapsulation, the pigment particles are sprayed with the polymer or with a solution containing the polymer and dried, or the pigment particles are immersed and treated in the polymer or polymer-containing liquid. The pigment particles are optionally precipitated, for example by changing the pH or adding a solvent, filtered off and dried, or spray dried.

たとえば、後に続く重合反応の前に、顔料を重合性のモノマーまたはモノマー混合物に添加することにより、エマルション重合中または懸濁液重合中に「その場で」顔料粒子をポリマー中に封入することもできる。   For example, pigment particles can be encapsulated “in situ” during emulsion or suspension polymerization by adding the pigment to the polymerizable monomer or monomer mixture prior to the subsequent polymerization reaction. it can.

処理する顔料に対するポリマーの量を、顔料の重量に基づいて、３〜５００重量％、好ましくは５０〜３００重量％の広い範囲内で変えることができる。   The amount of polymer relative to the pigment to be treated can vary within a wide range of 3 to 500% by weight, preferably 50 to 300% by weight, based on the weight of the pigment.

本発明は、高分子量の有機材料と、少なくとも１種の本発明による顔料組成物の着色有効量とを互いに混合する、着色プラスチックまたは着色ポリマー粒子の製造方法にも関する。   The invention also relates to a process for producing colored plastic or colored polymer particles, wherein a high molecular weight organic material and a coloring effective amount of at least one pigment composition according to the invention are mixed together.

本発明による顔料組成物を用いる高分子量の有機物質の着色は、たとえば、ロールミルまたは混合もしくは粉砕装置を用いて、このような顔料組成物を基材に混合することにより実施され、この結果、顔料組成物は高分子量の材料中に細かく分布する。混合した顔料組成物を含む高分子量の有機材料を、次いでそれ自体公知の方法、たとえばカレンダリング、圧縮成形、押出、塗布、スピニング、キャスティングによりまたは射出成形により加工し、これにより着色材料がその最終形状をもたらす。たとえば、固体、たとえば粉体の顔料組成物と、同時に粒状または粉末状の高分子量の有機材料とを、場合によりさらなる成分、たとえば添加剤も、加工直前に混合を行う押出機の取り入れ域に、直接に連続的に供給することにより、顔料組成物の混和を、実際の加工工程の直前に行うこともできる。しかし、通常、より均一な着色生成物を実現することができるので、顔料組成物を高分子量の有機材料に前もって混合するのが好ましい。   The coloring of high molecular weight organic substances using the pigment composition according to the invention is carried out by mixing such a pigment composition into a substrate, for example using a roll mill or a mixing or grinding device, so that the pigment The composition is finely distributed in the high molecular weight material. The high molecular weight organic material containing the mixed pigment composition is then processed in a manner known per se, for example by calendering, compression molding, extrusion, coating, spinning, casting or by injection molding, whereby the colored material is brought to its final Bring shape. For example, a solid, for example, powdered pigment composition, and at the same time a granular or powdery high molecular weight organic material, and optionally further components, such as additives, in the intake area of the extruder where it is mixed just prior to processing, By directly feeding continuously, the pigment composition can be mixed immediately before the actual processing step. However, it is usually preferred that the pigment composition is premixed with the high molecular weight organic material since a more uniform colored product can be achieved.

軟質の成形品を得るため、またはその脆性を減らすために、成形に先立っていわゆる可塑剤を高分子量の化合物に添加することが多くの場合望ましい。可塑剤として、たとえば、リン酸、フタル酸またはセバシン酸のエステルを用いることができる。本発明による方法では、着色剤の添加の前または後に、可塑剤をポリマーに添加することができる。異なる色合いを実現するために、高分子量の有機材料に、本発明による顔料組成物のほかに、場合により別のさらなる成分、たとえば充填剤またはドライヤー（乾燥剤）と共に、別の顔料または他の着色剤を所望の量で添加することも可能である。   It is often desirable to add a so-called plasticizer to the high molecular weight compound prior to molding in order to obtain a soft molded product or to reduce its brittleness. As the plasticizer, for example, an ester of phosphoric acid, phthalic acid or sebacic acid can be used. In the process according to the invention, the plasticizer can be added to the polymer before or after the addition of the colorant. In order to achieve different shades, high molecular weight organic materials can be combined with other pigments or other colorings, in addition to the pigment composition according to the invention, optionally with further further components, for example fillers or driers (drying agents). It is also possible to add the agent in the desired amount.

本発明による着色に適切な好ましい高分子量の有機材料は、ごく一般的に、誘電率が２．５以上であるポリマー、特にポリエステル（たとえばＰＥＴ）、ポリカーボネート（ＰＣ）、ポリスチレン（ＰＳ）、ポリメチルメタクリレート（ＰＭＭＡ）、ポリアミド、ポリエチレン、ポリプロピレン、スチレン／アクリロニトリル（ＳＡＮ）およびアクリロニトリル／ブタジエン／スチレン（ＡＢＳ）である。   Preferred high molecular weight organic materials suitable for coloring according to the invention are very generally polymers having a dielectric constant of 2.5 or more, in particular polyesters (eg PET), polycarbonate (PC), polystyrene (PS), polymethyl. Methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene / acrylonitrile (SAN) and acrylonitrile / butadiene / styrene (ABS).

ポリエステルが特に好ましく、ポリアミド、たとえばポリアミド６、ポリアミド６．６、ポリアミド１２およびアラミドが、さらに特に好ましい。   Polyesters are particularly preferred, and polyamides such as polyamide 6, polyamide 6.6, polyamide 12 and aramid are even more particularly preferred.

本発明による顔料組成物は、使用中の堅牢性が極めて良好である強く着色されたむらのない色相を持ち、特に、良好な耐光堅牢度および良好な熱安定性を持ち、機械的特性の低下が全くない上述の材料、特にポリアミド材料を提供する。   The pigment composition according to the invention has a strongly colored and even hue with very good fastness in use, in particular with good light fastness and good thermal stability and reduced mechanical properties. There is provided the above materials, in particular polyamide materials, which are completely absent.

以下、実施例により本発明を具体的に説明する。特記しない限り、部は重量部であり、％は重量％である。温度は℃で示す。重量部と容量部の関係はgとcm3の関係と同じである。 Hereinafter, the present invention will be described specifically by way of examples. Unless indicated otherwise, parts are parts by weight and percentages are percentages by weight. Temperature is shown in ° C. The relation between the weight part and the capacity part is the same as the relation between g and cm 3 .

実施例１：
式： Example 1:
formula:

Figure 2008536992
Figure 2008536992

の顔料の湿った５４％プレスケーク９．２５gを、水９５mLに分散させ、次いでTriameen（登録商標）OV［オレイルジプロピレントリアミン（AKZO Nobel）］１．５mLを加えた。懸濁液をさらに２時間攪拌し、次いでろ過した。吸引フィルター中の材料を水で洗浄し、１００mbarの真空下６０℃で乾燥した。 9.25 g of a wet 54% presscake of the pigment of was dispersed in 95 mL of water, followed by addition of 1.5 mL of Triameen® OV [AKZO Nobel]. The suspension was stirred for an additional 2 hours and then filtered. The material in the suction filter was washed with water and dried at 60 ° C. under 100 mbar vacuum.

実施例２：
式（３）の顔料の湿った５４％プレスケーク９．２５gを、水９５mLに分散させ、次いでTetrameen（登録商標）OV［オレイルトリプロピレンテトラミン（AKZO Nobel）］１．５mLを加えた。懸濁液をさらに２時間攪拌し、次いでろ過した。吸引フィルター中の材料を水で洗浄し、１００mbarの真空下６０℃で乾燥した。 Example 2:
9.25 g of a wet 54% presscake of the pigment of formula (3) was dispersed in 95 mL of water and then 1.5 mL of Tetrameen® OV [AKOL Nobel] was added. The suspension was stirred for an additional 2 hours and then filtered. The material in the suction filter was washed with water and dried at 60 ° C. under 100 mbar vacuum.

実施例３：
式（３）の顔料の湿った４６％プレスケーク２０．７gおよびポリアクリルアミド（ALDRICH CAS 9003-05-8）の５０％水溶液１０．７gを、水１５０mLに分散させた。懸濁液をBUCHI Mini Spray Dryer（Ｔi１３０〜１３２℃、Ｔa８０〜９０℃）中で乾燥した。（Ｔi＝入口温度、Ｔa＝出口温度）。 Example 3:
20.7 g of a moist 46% presscake of the pigment of formula (3) and 10.7 g of a 50% aqueous solution of polyacrylamide (ALDRICH CAS 9003-05-8) were dispersed in 150 mL of water. The suspension BUCHI Mini Spray Dryer (T i 130~132 ℃, T a 80~90 ℃) was dried in. (T i = inlet temperature, T a = outlet temperature).

実施例４：
式（３）の顔料の湿った４６％プレスケーク２０．７gおよびポリアクリルアミド（ALDRICH CAS 9003-05-8）の５０％水溶液４２．８gを、水１５０mLに分散させた。懸濁液をBUCHI Mini Spray Dryer中で乾燥した。 Example 4:
20.7 g of a wet 46% presscake of the pigment of formula (3) and 42.8 g of a 50% aqueous solution of polyacrylamide (ALDRICH CAS 9003-05-8) were dispersed in 150 mL of water. The suspension was dried in a BUCHI Mini Spray Dryer.

実施例５：
式（３）の顔料の湿った４６％プレスケーク２０．０gおよびＮＨ4−ポリアクリレートの４０％水溶液（Dispex（登録商標）A40、CIBA SC）２３．０gを、水２００mLに分散させた。次いで懸濁液を６０℃で１時間加熱し、続いてBUCHI Mini Spray Dryer中で乾燥した。 Example 5:
20.0 g of a moist 46% presscake of the pigment of formula (3) and 23.0 g of a 40% aqueous solution of NH 4 -polyacrylate (Dispex® A40, CIBA SC) were dispersed in 200 mL of water. The suspension was then heated at 60 ° C. for 1 hour and subsequently dried in a BUCHI Mini Spray Dryer.

実施例６：
式（３）の顔料の湿った３５％プレスケーク１５１．２gおよびスチレン／ポリアクリレートコポリマー（Narlex（登録商標）ex. National Starch）の３５％水溶液２８５．７gを水２Lに分散させた。懸濁液をBUCHI Mini Spray Dryer（Ｔi１５０℃、Ｔa８０〜７８℃）中で乾燥した。 Example 6:
151.2 g of wet 35% presscake of pigment of formula (3) and 285.7 g of 35% aqueous solution of styrene / polyacrylate copolymer (Narlex® ex. National Starch) were dispersed in 2 L of water. The suspension BUCHI Mini Spray Dryer (T i 150 ℃, T a 80~78 ℃) was dried in.

実施例７：
式（３）の顔料の湿った４８％プレスケーク１１．２gおよびスチレン／ポリアクリレートコポリマー（Narlex（登録商標）ex. National Starch）３５％水溶液２９．１gを、水４００mLに分散させた。塩酸溶液１０mLを用いて、ポリマーを沈殿させた。懸濁液をろ過し、乾燥した。 Example 7:
11.2 g of a wet 48% presscake of the pigment of formula (3) and 29.1 g of a 35% aqueous solution of styrene / polyacrylate copolymer (Narlex® ex. National Starch) were dispersed in 400 mL of water. The polymer was precipitated using 10 mL of hydrochloric acid solution. The suspension was filtered and dried.

実施例８：
式（３）の顔料の湿った４３％プレスケーク２５．５gおよび酢酸ブチル／ｓ−ブタノール中の変性ポリアクリレート４０％溶液（EFKA（登録商標）4400）５０．４gを、水４００mLに分散させた。懸濁液を真空キャビネット中、１００℃で乾燥した。 Example 8:
25.5 g of a wet 43% presscake of the pigment of formula (3) and 50.4 g of a modified polyacrylate 40% solution (EFKA® 4400) in butyl acetate / s-butanol were dispersed in 400 mL of water. . The suspension was dried at 100 ° C. in a vacuum cabinet.

実施例９：
押出機中、実施例１〜８の生成物０．２gを、いずれの場合もポリアミド６（Grillon（登録商標）F47、EMS Chemie）９９．８gで分散させた。チルロールによって、ペーストをフィルムに形成した。 Example 9:
In the extruder, 0.2 g of the product of Examples 1 to 8 was dispersed with 99.8 g of polyamide 6 (Grillon® F47, EMS Chemie) in each case. The paste was formed into a film by chill roll.

式（３）の未処理の顔料を含有する対照の着色フィルムが強く蛍光を発したのに対して、本発明の着色フィルムは全て蛍光を伴わない赤色のままであった。   The control colored film containing the untreated pigment of formula (3) was highly fluorescent, whereas all of the colored films of the present invention remained red with no fluorescence.

実施例１０：
式（３）の顔料１０．０gをアセトン中のポリスチレンの１％溶液１０００mLに分散させ、水２０００mLに滴下した。次いで懸濁液をろ過し、乾燥した。 Example 10:
10.0 g of the pigment of formula (3) was dispersed in 1000 mL of a 1% solution of polystyrene in acetone and added dropwise to 2000 mL of water. The suspension was then filtered and dried.

実施例１１：
式（７）の顔料の湿った６２％プレスケーク４７．０gおよびＮＨ4−ポリアクリレートコポリマーの４０％水溶液（Dispex（登録商標）GA40、CIBA SC製）１５．０gを、水６００mLに分散させた。懸濁液をBUCHI Mini Spray Dryer中で乾燥した。 Example 11:
47.0 g of a wet 62% presscake of the pigment of formula (7) and 15.0 g of a 40% aqueous solution of NH 4 -polyacrylate copolymer (Dispex® GA40, manufactured by CIBA SC) were dispersed in 600 mL of water. . The suspension was dried in a BUCHI Mini Spray Dryer.

実施例１２：
プテリジン顔料CI PY 215の湿った４２％プレスケーク２３．７gおよびポリアクリル酸ナトリウムの４０％水溶液（Dispex（登録商標）GA40、CIBA SC製）５１．０gを、水２００mLに分散させた。次いで、ジココジメチルアンモニウムクロリドのイソプロパノール／水７５％溶液（Arquad（登録商標）2C-75、AKZO NOBEL製）２５mLを添加することにより、ポリマーを沈殿させ、続いてろ別し、乾燥した。 Example 12:
23.7 g of a moist 42% presscake of pteridine pigment CI PY 215 and 51.0 g of a 40% aqueous solution of sodium polyacrylate (Dispex® GA40, manufactured by CIBA SC) were dispersed in 200 mL of water. The polymer was then precipitated by adding 25 mL of an isopropanol / water 75% solution of dicocodimethylammonium chloride (Arquad® 2C-75, manufactured by AKZO NOBEL), followed by filtration and drying.

実施例１３：
式（３）の顔料１０．０gおよびトルエン−２，４−ジイソシアネート７．５gを、アセトン３００mLに５５℃で分散させ、次いでこのジイソシアネートを１，２−ブタンジオール３．０gと５５℃で２時間重合した。次いでこの懸濁液をろ過し、乾燥した。 Example 13:
10.0 g of the pigment of formula (3) and 7.5 g of toluene-2,4-diisocyanate are dispersed in 300 mL of acetone at 55 ° C., and then the diisocyanate is added with 3.0 g of 1,2-butanediol at 55 ° C. for 2 hours. Polymerized. The suspension was then filtered and dried.

実施例１４：
プテリジン顔料CI PY 215の湿った４５．１％プレスケーク４４．３gおよびポリアクリレートの５０％水溶液（Dispex（登録商標）R50、CIBA SC製）２１．０gを、水２００mLに分散させた。次いでこの懸濁液を、水酸化カルシウムの１０％水溶液１０００mLに滴下し、続いてろ過し、乾燥した。 Example 14:
44.3 g of wet 45.1% presscake of pteridine pigment CI PY 215 and 21.0 g of a 50% aqueous solution of polyacrylate (Dispex® R50, manufactured by CIBA SC) were dispersed in 200 mL of water. This suspension was then added dropwise to 1000 mL of a 10% aqueous solution of calcium hydroxide, followed by filtration and drying.

Claims (10)

顔料（Ａ）を含む顔料組成物であって、顔料（Ａ）が、オリゴマーもしくはポリマーのアミンで処理されたか、またはポリマー中に封入されている、顔料組成物。   A pigment composition comprising a pigment (A), wherein the pigment (A) is treated with an oligomer or polymer amine or encapsulated in a polymer. 顔料（Ａ）が、ジケトピロロピロール、アゾ、キナクリドン、キノフタロン、フタロシアニン、インダントロン、フラバントロン、ピラントロン、アントラキノン、ペリレン、ジオキサジン、ペリノン、チオインジゴ、イソインドリン、プテリジン、イソインドリノンまたは金属錯体顔料である、請求項１記載の顔料組成物。   Pigment (A) is diketopyrrolopyrrole, azo, quinacridone, quinophthalone, phthalocyanine, indanthrone, flavantron, pyrantrone, anthraquinone, perylene, dioxazine, perinone, thioindigo, isoindoline, pteridine, isoindolinone or metal complex pigment The pigment composition according to claim 1. オリゴマーもしくはポリマーのアミンとして、ポリエチレンイミン、アルキルジエチレントリアミン、アルキルトリエチレンテトラミン、アルキルジプロピレントリアミン、アルキルトリプロピレンテトラミン、アルコキシトリアミン、アルコキシテトラミンまたはビニルアミンポリマー類の化合物を用いる、請求項１および２記載の顔料組成物。   3. The compound according to claim 1, wherein the oligomer or polymer amine is a polyethyleneimine, alkyldiethylenetriamine, alkyltriethylenetetramine, alkyldipropylenetriamine, alkyltripropylenetetramine, alkoxytriamine, alkoxytetramine or vinylamine polymer compound. Pigment composition. 封入用ポリマーとして、天然産物、または重合、重付加もしくは重縮合の合成生成物、たとえばポリエステル、ポリエーテル、ポリアミド、ポリイミド、ポリ尿素、ポリウレタン、ポリスルフィド、ポリオレフィン、ポリ（メタ）アクリレート、ポリ（メタ）アクリルアミド、ポリ酢酸ビニル、ポリエチレンイミン、ポリアミン、ポリアルコール、ポリグリコール、ポリグリコールエステル、ポリカルボン酸、ポリスチレン、または上述したポリマーを含有する混合ポリマー、またはコポリマーもしくはターポリマーを用いる、請求項１および２記載の顔料組成物。   As encapsulating polymers, natural products or synthetic products of polymerization, polyaddition or polycondensation, such as polyester, polyether, polyamide, polyimide, polyurea, polyurethane, polysulfide, polyolefin, poly (meth) acrylate, poly (meth) 1 and 2 using acrylamide, polyvinyl acetate, polyethyleneimine, polyamine, polyalcohol, polyglycol, polyglycol ester, polycarboxylic acid, polystyrene, or mixed polymers or copolymers or terpolymers containing the aforementioned polymers. The pigment composition described. 封入用ポリマーとして、ポリアクリル酸アンモニウム、ナトリウム、カルシウム、アルミニウム、亜鉛もしくはジルコニウム、アクリル酸エステルまたは（メタ）アクリル酸／スチレンコポリマーを用いる、請求項４記載の顔料組成物。   5. A pigment composition according to claim 4, wherein the encapsulating polymer is ammonium polyacrylate, sodium, calcium, aluminum, zinc or zirconium, an acrylate ester or a (meth) acrylic acid / styrene copolymer. 顔料粒子を、オリゴマーもしくはポリマーのアミンそれ自体と共に、またはそのアミンを含有する溶液と共にスプレーし、乾燥するか、あるいは顔料粒子をオリゴマーもしくはポリマーのアミンまたはオリゴマーもしくはポリマーのアミンを含有する液体に浸漬し、処理した顔料粒子をろ別し乾燥するか、またはスプレー乾燥する、請求項１記載の顔料組成物の製造。   The pigment particles are sprayed with the oligomer or polymer amine itself or with a solution containing the amine and dried, or the pigment particles are immersed in a liquid containing the oligomer or polymer amine or oligomer or polymer amine. 2. The production of a pigment composition according to claim 1, wherein the treated pigment particles are filtered and dried, or spray-dried. 顔料粒子をポリマー単独またはそのポリマーを含有する溶液と共にスプレーし、次いで乾燥するか、あるいは顔料粒子をポリマーまたはポリマーを含有する液体に浸漬し、処理した顔料粒子を場合により、たとえばｐＨの変更または溶剤の添加によって沈殿させ、ろ別し乾燥するか、またはスプレー乾燥する、請求項１記載の顔料組成物の製造。   The pigment particles are sprayed with the polymer alone or with a solution containing the polymer and then dried, or the pigment particles are immersed in the polymer or a liquid containing the polymer and the treated pigment particles are optionally treated, for example, with a pH change or solvent The pigment composition according to claim 1, wherein the pigment composition is precipitated by filtration, filtered and dried, or spray-dried. 高分子量の有機材料と、少なくとも１種の請求項１記載の顔料組成物の着色有効量とを互いに混合する、着色プラスチックまたは着色ポリマー粒子の製造方法。   A method for producing colored plastic or colored polymer particles, wherein a high molecular weight organic material and at least one coloring effective amount of the pigment composition according to claim 1 are mixed with each other. 着色プラスチックまたは着色ポリマー粒子の製造における、請求項１記載の顔料組成物の使用。   Use of the pigment composition according to claim 1 in the production of colored plastic or colored polymer particles. 請求項１記載の顔料組成物を用いて着色した、プラスチックおよび着色ポリマー粒子。   Plastic and colored polymer particles colored with the pigment composition of claim 1.
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